Cyclodextrin Chemistry: Synthesis of Amphiphilic Fluorescent Glycodendrimers and Development of Acid-mediated O-desilylation Methodology
Date
2015-09-17
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Abstract
Cyclodextrins (CDs) constitute a group of D-glucose-based host molecules with a hydrophobic cavity that can be used to form inclusion complexes with organic compounds. The Ling group has developed a group of amphiphilic glycodendrimers which have been shown to self-assemble into nanoparticles in water, and such systems have been confirmed to deliver anticancer medicines into cancer cells. To further study the cellular uptake mechanism, the present thesis work concerns the design and synthesis of a class of amphiphilic CD-based glycodendrimers containing a fluorophore. NBD was chosen as the fluorophore because it is small and non-ionic. The DIBAL-H reagent allowed a two-fold differentiation of primary hydroxyl groups of the CD molecules, which facilitated the sequential addition of NBD and of sugar moieties. A novel acid-catalyzed O-desilylation methodology has also been developed from this thesis work using the easily accessible per-3,6-O-silylated CD substrates in a mixture of methanol-chloroform.
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Chemistry--Organic
Citation
Chen, T. (2015). Cyclodextrin Chemistry: Synthesis of Amphiphilic Fluorescent Glycodendrimers and Development of Acid-mediated O-desilylation Methodology (Master's thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca. doi:10.11575/PRISM/25509